tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((5-octylindolin-1-yl)methyl)propane-1,3-diol

HRID 710289Notes

Reaction equation

HRID 710289 reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:26]C(=O)OC(C)(C)C)([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH2:4][O:3]1.CC1(C)OCC(NC(=O)OC(C)(C)C)(CNC2C=CC(CCCCCCCC)=CC=2)CO1>>[NH2:26][C:5]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)([CH2:6][OH:7])[CH2:4][OH:3]

Participants

3

Reactant 2

HCID 66726563tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamateHCID 86661758tert-Butyl 2,2-dimethyl-5-((5-octylindolin-1-yl)methyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461947452-Amino-2-((5-octylindolin-1-yl)methyl)propane-1,3-diolYield 71%

Procedure

When the product of Step D was substituted for tert-butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate in Example 1, Step B, the identical process afforded the title compound in 71% yield., as colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.84 Hz); 1.26 (m, 10H); 1.52 (m, 2H); 2.17 (broad s, 4H); 2.47 (tr, 2H, J=7.92 Hz); 2.94 (tr, 2H, J=8.1 Hz); 3.04 (s, 2H); 3.42 (tr, 2H, J=8.1 Hz); 3.58 (s, 4H); 6.53 (d, 1H, J=7.92 Hz); 6.87 (d, 1H, J=7.92 Hz); 6.91 (s, 1H).

Sources & evidence

ORD record
ord-70c85692c13440f69446eb2c6feaf2f7
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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